Triethylamine → 4-Chloroquinazoline-6-carboxylic acid methoxymethylamide
Reaction equation
[CH3:1][O:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][N:11]=[C:10]2O)=[O:6].C(N(CC)CC)C.P(Cl)(Cl)([Cl:27])=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][N:11]=[C:10]2[Cl:27])=[O:6]Participants
Conditions
- Temperature
- 130 °C
Procedure
4-Hydroxyquinazoline-6-carboxylic acid methoxymethylamide (XIII-1, 2.9 g) was suspended in toluene (57 ml), and 6.8 ml of triethylamine and 3.4 ml of phosphorus oxychloride were added, followed by stirring at 130° C. for 30 minutes. After completion of the reaction, the reaction mixture was cooled to room temperature, and 50 ml of aqueous saturated sodium bicarbonate solution and ethyl acetate were added. Sodium bicarbonate was added until the aqueous layer exhibited a pH 8, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate solution, dried over sodium sulfate. After concentration, the crystalline residue was washed with diethyl ether, and dried to obtain 4-chloroquinazoline-6-carboxylic acid methoxymethylamide (XIV-1, 2.3 g) as a white solid.
Workup
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled to room temperature
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with aqueous saturated sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- concentrationAfter concentration
- washthe crystalline residue was washed with diethyl ether
- customdried
Sources & evidence
- ORD record
- ord-6fe4313276964d158ebaf1f746689949
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202879B2
Reaction notes
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